IL275084B2 - Triazolobenzazepines as vasopressin v1a receptor antagonists - Google Patents
Triazolobenzazepines as vasopressin v1a receptor antagonistsInfo
- Publication number
- IL275084B2 IL275084B2 IL275084A IL27508420A IL275084B2 IL 275084 B2 IL275084 B2 IL 275084B2 IL 275084 A IL275084 A IL 275084A IL 27508420 A IL27508420 A IL 27508420A IL 275084 B2 IL275084 B2 IL 275084B2
- Authority
- IL
- Israel
- Prior art keywords
- triazolo
- chloro
- dihydro
- cyclohexyl
- pyridin
- Prior art date
Links
- 239000002464 receptor antagonist Substances 0.000 title claims 2
- 229940044551 receptor antagonist Drugs 0.000 title claims 2
- 102000004136 Vasopressin Receptors Human genes 0.000 title 1
- 108090000643 Vasopressin Receptors Proteins 0.000 title 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 187
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 73
- 150000001875 compounds Chemical class 0.000 claims 47
- 229910052736 halogen Inorganic materials 0.000 claims 39
- 150000002367 halogens Chemical group 0.000 claims 39
- 229910052739 hydrogen Inorganic materials 0.000 claims 36
- 239000001257 hydrogen Substances 0.000 claims 36
- 125000000623 heterocyclic group Chemical group 0.000 claims 33
- DQFQCHIDRBIESA-UHFFFAOYSA-N 1-benzazepine Chemical compound N1C=CC=CC2=CC=CC=C12 DQFQCHIDRBIESA-UHFFFAOYSA-N 0.000 claims 31
- 125000003118 aryl group Chemical group 0.000 claims 27
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 26
- 125000004043 oxo group Chemical group O=* 0.000 claims 23
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 21
- 125000000753 cycloalkyl group Chemical group 0.000 claims 20
- 125000001072 heteroaryl group Chemical group 0.000 claims 15
- 229910052757 nitrogen Inorganic materials 0.000 claims 15
- 150000002431 hydrogen Chemical group 0.000 claims 9
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 9
- 239000000460 chlorine Chemical group 0.000 claims 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 7
- 239000013543 active substance Substances 0.000 claims 6
- 229910052801 chlorine Inorganic materials 0.000 claims 6
- 150000003839 salts Chemical class 0.000 claims 6
- 239000012453 solvate Substances 0.000 claims 6
- 125000001309 chloro group Chemical group Cl* 0.000 claims 5
- 201000010099 disease Diseases 0.000 claims 5
- 125000005842 heteroatom Chemical group 0.000 claims 5
- 229910052760 oxygen Inorganic materials 0.000 claims 5
- 229910052717 sulfur Inorganic materials 0.000 claims 5
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 4
- 229910052794 bromium Inorganic materials 0.000 claims 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
- 230000002093 peripheral effect Effects 0.000 claims 4
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims 4
- 229920006395 saturated elastomer Polymers 0.000 claims 4
- WAYZQLIRXHPOCN-UHFFFAOYSA-N 5,6-dihydro-4h-[1,2,4]triazolo[4,3-a][1]benzazepine Chemical group C1CCC2=NN=CN2C2=CC=CC=C21 WAYZQLIRXHPOCN-UHFFFAOYSA-N 0.000 claims 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 3
- 125000002837 carbocyclic group Chemical group 0.000 claims 3
- 208000035475 disorder Diseases 0.000 claims 3
- CKJNUZNMWOVDFN-UHFFFAOYSA-N methanone Chemical compound O=[CH-] CKJNUZNMWOVDFN-UHFFFAOYSA-N 0.000 claims 3
- 239000000203 mixture Substances 0.000 claims 3
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims 3
- 238000011321 prophylaxis Methods 0.000 claims 3
- -1 t-butyl [8-chloro-1-[1-(pyridin-2-yl)piperidin-4-yl]-5,6-dihydro-4 H-[1,2,4]triazolo[4,3-a][1]benzazepin-5-yl] carbamate Chemical class 0.000 claims 3
- DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 3
- 238000011282 treatment Methods 0.000 claims 3
- 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 2
- 208000019901 Anxiety disease Diseases 0.000 claims 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 2
- 230000016571 aggressive behavior Effects 0.000 claims 2
- 230000003556 anti-epileptic effect Effects 0.000 claims 2
- 239000001961 anticonvulsive agent Substances 0.000 claims 2
- 229960003965 antiepileptics Drugs 0.000 claims 2
- 229940030600 antihypertensive agent Drugs 0.000 claims 2
- 239000002220 antihypertensive agent Substances 0.000 claims 2
- 230000036506 anxiety Effects 0.000 claims 2
- 125000002619 bicyclic group Chemical group 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 239000003795 chemical substances by application Substances 0.000 claims 2
- RWTNPBWLLIMQHL-UHFFFAOYSA-N fexofenadine Chemical group C1=CC(C(C)(C(O)=O)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 RWTNPBWLLIMQHL-UHFFFAOYSA-N 0.000 claims 2
- 125000002950 monocyclic group Chemical group 0.000 claims 2
- 125000002911 monocyclic heterocycle group Chemical group 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims 2
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims 2
- 229940035680 psychoanaleptics Drugs 0.000 claims 2
- 229940035677 psycholeptics Drugs 0.000 claims 2
- 230000002048 spasmolytic effect Effects 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- JSEYAPGSGXYHIJ-UHFFFAOYSA-N 1'-(8-chloro-5-methoxy-5,6-dihydro-4H-[1,2,4]triazolo[4,3-a][1]benzazepin-1-yl)spiro[1H-2-benzofuran-3,4'-piperidine] Chemical compound ClC=1C=CC2=C(CC(CC=3N2C(=NN3)N3CCC2(CC3)OCC3=C2C=CC=C3)OC)C1 JSEYAPGSGXYHIJ-UHFFFAOYSA-N 0.000 claims 1
- AGRIQBHIKABLPJ-UHFFFAOYSA-N 1-Pyrrolidinecarboxaldehyde Chemical compound O=CN1CCCC1 AGRIQBHIKABLPJ-UHFFFAOYSA-N 0.000 claims 1
- MLIREBYILWEBDM-UHFFFAOYSA-M 2-cyanoacetate Chemical compound [O-]C(=O)CC#N MLIREBYILWEBDM-UHFFFAOYSA-M 0.000 claims 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- PLRCVBKYFLWAAT-UHFFFAOYSA-N 3,3-difluorocyclobutane-1-carboxylic acid Chemical compound OC(=O)C1CC(F)(F)C1 PLRCVBKYFLWAAT-UHFFFAOYSA-N 0.000 claims 1
- HYIUDFLDFSIXTR-UHFFFAOYSA-N 4,4-difluorocyclohexane-1-carboxylic acid Chemical compound OC(=O)C1CCC(F)(F)CC1 HYIUDFLDFSIXTR-UHFFFAOYSA-N 0.000 claims 1
- JQTMGOLZSBTZMS-UHFFFAOYSA-N 4-methylpiperazine-1-carbaldehyde Chemical compound CN1CCN(C=O)CC1 JQTMGOLZSBTZMS-UHFFFAOYSA-N 0.000 claims 1
- KIFRZXVXNQREGA-UHFFFAOYSA-N 8'-chloro-1'-(1-pyrimidin-2-ylazetidin-3-yl)spiro[1,3-dioxolane-2,5'-4,6-dihydro-[1,2,4]triazolo[4,3-a][1]benzazepine] Chemical compound ClC=1C=CC2=C(CC3(CC=4N2C(=NN4)C4CN(C4)C4=NC=CC=N4)OCCO3)C1 KIFRZXVXNQREGA-UHFFFAOYSA-N 0.000 claims 1
- WCUZKFFWOPTWGC-UHFFFAOYSA-N 8'-chloro-1'-(4-piperidin-1-ylpiperidin-1-yl)spiro[1,3-dioxolane-2,5'-4,6-dihydro-[1,2,4]triazolo[4,3-a][1]benzazepine] Chemical compound N1(CCCCC1)C1CCN(CC1)C1=NN=C2N1C1=C(CC3(C2)OCCO3)C=C(C=C1)Cl WCUZKFFWOPTWGC-UHFFFAOYSA-N 0.000 claims 1
- BEMGGBQAFLIMHD-INIZCTEOSA-N 8'-chloro-1'-[(3S)-1-(pyridin-2-ylmethyl)pyrrolidin-3-yl]spiro[1,3-dioxolane-2,5'-4,6-dihydro-[1,2,4]triazolo[4,3-a][1]benzazepine] Chemical compound ClC=1C=CC2=C(CC3(CC=4N2C(=NN4)[C@@H]4CN(CC4)CC4=NC=CC=C4)OCCO3)C1 BEMGGBQAFLIMHD-INIZCTEOSA-N 0.000 claims 1
- BEMGGBQAFLIMHD-UHFFFAOYSA-N 8'-chloro-1'-[1-(pyridin-2-ylmethyl)pyrrolidin-3-yl]spiro[1,3-dioxolane-2,5'-4,6-dihydro-[1,2,4]triazolo[4,3-a][1]benzazepine] Chemical compound ClC=1C=CC2=C(CC3(CC=4N2C(=NN4)C4CN(CC4)CC4=NC=CC=C4)OCCO3)C1 BEMGGBQAFLIMHD-UHFFFAOYSA-N 0.000 claims 1
- HHUJZNAZACMNKH-UHFFFAOYSA-N 8'-chloro-1'-[1-(pyridin-3-ylmethyl)pyrrolidin-3-yl]spiro[1,3-dioxolane-2,5'-4,6-dihydro-[1,2,4]triazolo[4,3-a][1]benzazepine] Chemical compound ClC=1C=CC2=C(CC3(CC=4N2C(=NN4)C4CN(CC4)CC=4C=NC=CC4)OCCO3)C1 HHUJZNAZACMNKH-UHFFFAOYSA-N 0.000 claims 1
- OYPUURFAOBBZMP-UHFFFAOYSA-N 8'-chloro-1'-[4-(3-chloropyridin-2-yl)piperazin-1-yl]spiro[1,3-dioxolane-2,5'-4,6-dihydro-[1,2,4]triazolo[4,3-a][1]benzazepine] Chemical compound ClC=1C=CC2=C(CC3(CC=4N2C(=NN4)N4CCN(CC4)C4=NC=CC=C4Cl)OCCO3)C1 OYPUURFAOBBZMP-UHFFFAOYSA-N 0.000 claims 1
- MQXLYIKREIXAEQ-UHFFFAOYSA-N 8'-chloro-1'-spiro[1H-2-benzofuran-3,4'-piperidine]-1'-ylspiro[1,3-dioxolane-2,5'-4,6-dihydro-[1,2,4]triazolo[4,3-a][1]benzazepine] Chemical compound ClC=1C=CC2=C(CC3(CC=4N2C(=NN4)N4CCC2(CC4)OCC4=C2C=CC=C4)OCCO3)C1 MQXLYIKREIXAEQ-UHFFFAOYSA-N 0.000 claims 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims 1
- MJAZJWNDROEKLZ-UHFFFAOYSA-N 8-chloro-1-(3,3-difluorocyclobutyl)-N-propan-2-yl-5,6-dihydro-4H-[1,2,4]triazolo[4,3-a][1]benzazepin-5-amine Chemical compound ClC=1C=CC2=C(CC(CC=3N2C(=NN3)C3CC(C3)(F)F)NC(C)C)C1 MJAZJWNDROEKLZ-UHFFFAOYSA-N 0.000 claims 1
- PMWABJQCQUQUHR-UHFFFAOYSA-N 8-chloro-1-(4,4-difluorocyclohexyl)-N-propan-2-yl-5,6-dihydro-4H-[1,2,4]triazolo[4,3-a][1]benzazepin-5-amine Chemical compound ClC=1C=CC2=C(CC(CC=3N2C(=NN3)C3CCC(CC3)(F)F)NC(C)C)C1 PMWABJQCQUQUHR-UHFFFAOYSA-N 0.000 claims 1
- GQBXZAWMECECOS-UHFFFAOYSA-N 8-chloro-1-(4-pyridin-2-yloxypiperidin-1-yl)-5,6-dihydro-4H-[1,2,4]triazolo[4,3-a][1]benzazepin-5-ol Chemical compound OC1CC2=NN=C(N2C2=C(C1)C=C(Cl)C=C2)N1CCC(CC1)OC1=NC=CC=C1 GQBXZAWMECECOS-UHFFFAOYSA-N 0.000 claims 1
- BNQBQRFMXOGMSI-UHFFFAOYSA-N 8-chloro-1-spiro[1H-2-benzofuran-3,4'-piperidine]-1'-yl-4,6-dihydro-[1,2,4]triazolo[4,3-a][1]benzazepin-5-one Chemical compound ClC=1C=CC2=C(CC(CC=3N2C(=NN3)N3CCC2(CC3)OCC3=C2C=CC=C3)=O)C1 BNQBQRFMXOGMSI-UHFFFAOYSA-N 0.000 claims 1
- GRVPIDSKKZPVAA-UHFFFAOYSA-N 8-chloro-1-spiro[1H-2-benzofuran-3,4'-piperidine]-1'-yl-5,6-dihydro-4H-[1,2,4]triazolo[4,3-a][1]benzazepin-5-ol Chemical compound ClC=1C=CC2=C(CC(CC=3N2C(=NN3)N3CCC2(CC3)OCC3=C2C=CC=C3)O)C1 GRVPIDSKKZPVAA-UHFFFAOYSA-N 0.000 claims 1
- UDWXJDDCPSNETR-NYRJJRHWSA-N 8-chloro-5-methoxy-1-[(3R)-1-(pyridin-2-ylmethyl)pyrrolidin-3-yl]-5,6-dihydro-4H-[1,2,4]triazolo[4,3-a][1]benzazepine Chemical compound ClC=1C=CC2=C(CC(CC=3N2C(=NN3)[C@H]3CN(CC3)CC3=NC=CC=C3)OC)C1 UDWXJDDCPSNETR-NYRJJRHWSA-N 0.000 claims 1
- GYARJNRKOJFJCW-VTBWFHPJSA-N 8-chloro-5-methoxy-1-[(3R)-1-(pyridin-3-ylmethyl)pyrrolidin-3-yl]-5,6-dihydro-4H-[1,2,4]triazolo[4,3-a][1]benzazepine Chemical compound ClC=1C=CC2=C(CC(CC=3N2C(=NN3)[C@H]3CN(CC3)CC=3C=NC=CC3)OC)C1 GYARJNRKOJFJCW-VTBWFHPJSA-N 0.000 claims 1
- UDWXJDDCPSNETR-UHFFFAOYSA-N 8-chloro-5-methoxy-1-[1-(pyridin-2-ylmethyl)pyrrolidin-3-yl]-5,6-dihydro-4H-[1,2,4]triazolo[4,3-a][1]benzazepine Chemical compound ClC=1C=CC2=C(CC(CC=3N2C(=NN3)C3CN(CC3)CC3=NC=CC=C3)OC)C1 UDWXJDDCPSNETR-UHFFFAOYSA-N 0.000 claims 1
- CJYAZXOQOZQOSL-UHFFFAOYSA-N 8-chloro-N,N-dimethyl-1-spiro[1H-2-benzofuran-3,4'-piperidine]-1'-yl-5,6-dihydro-4H-[1,2,4]triazolo[4,3-a][1]benzazepin-5-amine Chemical compound ClC=1C=CC2=C(CC(CC=3N2C(=NN3)N3CCC2(CC3)OCC3=C2C=CC=C3)N(C)C)C1 CJYAZXOQOZQOSL-UHFFFAOYSA-N 0.000 claims 1
- QVRBVDNHXKKVJZ-UHFFFAOYSA-N 8-chloro-N-propan-2-yl-1-(1-pyridin-2-ylpiperidin-4-yl)-5,6-dihydro-4H-[1,2,4]triazolo[4,3-a][1]benzazepin-5-amine Chemical compound ClC=1C=CC2=C(CC(CC=3N2C(=NN3)C3CCN(CC3)C3=NC=CC=C3)NC(C)C)C1 QVRBVDNHXKKVJZ-UHFFFAOYSA-N 0.000 claims 1
- 206010000117 Abnormal behaviour Diseases 0.000 claims 1
- HHQNFEZHCJDCMD-UHFFFAOYSA-N COC1(C)CCC(CC1)c1nnc2CC(Cc3cc(Cl)ccc3-n12)NC(C)C Chemical compound COC1(C)CCC(CC1)c1nnc2CC(Cc3cc(Cl)ccc3-n12)NC(C)C HHQNFEZHCJDCMD-UHFFFAOYSA-N 0.000 claims 1
- PCBZRNYXXCIELG-WYFCWLEVSA-N COC1=CC=C(C[C@H](NC(=O)OC2CCCC3(C2)OOC2(O3)C3CC4CC(C3)CC2C4)C(=O)N[C@@H]2[C@@H](CO)O[C@H]([C@@H]2O)N2C=NC3=C2N=CN=C3N(C)C)C=C1 Chemical compound COC1=CC=C(C[C@H](NC(=O)OC2CCCC3(C2)OOC2(O3)C3CC4CC(C3)CC2C4)C(=O)N[C@@H]2[C@@H](CO)O[C@H]([C@@H]2O)N2C=NC3=C2N=CN=C3N(C)C)C=C1 PCBZRNYXXCIELG-WYFCWLEVSA-N 0.000 claims 1
- FWVNTNIQZHHZGW-UHFFFAOYSA-N COC1Cc2nnc(C3CCN(C3)C(=O)c3cccnc3)n2-c2ccc(Cl)cc2C1 Chemical compound COC1Cc2nnc(C3CCN(C3)C(=O)c3cccnc3)n2-c2ccc(Cl)cc2C1 FWVNTNIQZHHZGW-UHFFFAOYSA-N 0.000 claims 1
- CUJXTRXYZUGRGH-UHFFFAOYSA-N COC1Cc2nnc(C3CCN(CC3)C3CCOCC3)n2-c2ccc(Cl)cc2C1 Chemical compound COC1Cc2nnc(C3CCN(CC3)C3CCOCC3)n2-c2ccc(Cl)cc2C1 CUJXTRXYZUGRGH-UHFFFAOYSA-N 0.000 claims 1
- WIRPYLVADCJHBL-ZENAZSQFSA-N COC1Cc2nnc(C3CCN(CC3)[C@H]3CCOC3)n2-c2ccc(Cl)cc2C1 Chemical compound COC1Cc2nnc(C3CCN(CC3)[C@H]3CCOC3)n2-c2ccc(Cl)cc2C1 WIRPYLVADCJHBL-ZENAZSQFSA-N 0.000 claims 1
- UYSQEAPPBIMHCL-UHFFFAOYSA-N COC1Cc2nnc(N3CCN(CC3)c3ccccn3)n2-c2ccc(Cl)cc2C1 Chemical compound COC1Cc2nnc(N3CCN(CC3)c3ccccn3)n2-c2ccc(Cl)cc2C1 UYSQEAPPBIMHCL-UHFFFAOYSA-N 0.000 claims 1
- UDWXJDDCPSNETR-FUKCDUGKSA-N COC1Cc2nnc([C@H]3CCN(Cc4ccccn4)C3)n2-c2ccc(Cl)cc2C1 Chemical compound COC1Cc2nnc([C@H]3CCN(Cc4ccccn4)C3)n2-c2ccc(Cl)cc2C1 UDWXJDDCPSNETR-FUKCDUGKSA-N 0.000 claims 1
- GYARJNRKOJFJCW-UCFFOFKASA-N COC1Cc2nnc([C@H]3CCN(Cc4cccnc4)C3)n2-c2ccc(Cl)cc2C1 Chemical compound COC1Cc2nnc([C@H]3CCN(Cc4cccnc4)C3)n2-c2ccc(Cl)cc2C1 GYARJNRKOJFJCW-UCFFOFKASA-N 0.000 claims 1
- DHYXYWFGIXCEBM-UHFFFAOYSA-N CSC1=Nc2ccc(Cl)cc2CC(C1)NC(=O)OC(C)(C)C Chemical compound CSC1=Nc2ccc(Cl)cc2CC(C1)NC(=O)OC(C)(C)C DHYXYWFGIXCEBM-UHFFFAOYSA-N 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- OVQBNSTZHOMVGU-UHFFFAOYSA-N ClC=1C=CC2=C(CC(CC(N2)=O)OC)C=1 Chemical compound ClC=1C=CC2=C(CC(CC(N2)=O)OC)C=1 OVQBNSTZHOMVGU-UHFFFAOYSA-N 0.000 claims 1
- DJAFDCOYZMFSOL-UHFFFAOYSA-N ClC=1C=CC2=C(CC(CC(N2)=S)OC)C=1 Chemical compound ClC=1C=CC2=C(CC(CC(N2)=S)OC)C=1 DJAFDCOYZMFSOL-UHFFFAOYSA-N 0.000 claims 1
- JKGYRNAMDWRPGF-UHFFFAOYSA-N ClC=1C=CC2=C(CC(CC=3N2C(=NN=3)C2CCN(CC2)C2=NC=CC=C2)N)C=1 Chemical compound ClC=1C=CC2=C(CC(CC=3N2C(=NN=3)C2CCN(CC2)C2=NC=CC=C2)N)C=1 JKGYRNAMDWRPGF-UHFFFAOYSA-N 0.000 claims 1
- GYARJNRKOJFJCW-UHFFFAOYSA-N ClC=1C=CC2=C(CC(CC=3N2C(=NN=3)C2CN(CC2)CC=2C=NC=CC=2)OC)C=1 Chemical compound ClC=1C=CC2=C(CC(CC=3N2C(=NN=3)C2CN(CC2)CC=2C=NC=CC=2)OC)C=1 GYARJNRKOJFJCW-UHFFFAOYSA-N 0.000 claims 1
- LELXCCSRCZBJBZ-UHFFFAOYSA-N ClC=1C=CC2=C(CC(CC=3N2C(=NN=3)N2CCC(CC2)OC2=NC=CC=C2)OC)C=1 Chemical compound ClC=1C=CC2=C(CC(CC=3N2C(=NN=3)N2CCC(CC2)OC2=NC=CC=C2)OC)C=1 LELXCCSRCZBJBZ-UHFFFAOYSA-N 0.000 claims 1
- CTVXILDJPCHRPW-UHFFFAOYSA-N ClC=1C=CC2=C(CC(CC=3N2C(=NN=3)N2CCN(CC2)C2=NC=CC=C2Cl)OC)C=1 Chemical compound ClC=1C=CC2=C(CC(CC=3N2C(=NN=3)N2CCN(CC2)C2=NC=CC=C2Cl)OC)C=1 CTVXILDJPCHRPW-UHFFFAOYSA-N 0.000 claims 1
- KPCDLWYXDNOSBC-UHFFFAOYSA-N ClC=1C=CC2=C(CC3(CC=4N2C(=NN=4)N2CCN(CC2)C2=NC=CC=C2)OCCO3)C=1 Chemical compound ClC=1C=CC2=C(CC3(CC=4N2C(=NN=4)N2CCN(CC2)C2=NC=CC=C2)OCCO3)C=1 KPCDLWYXDNOSBC-UHFFFAOYSA-N 0.000 claims 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims 1
- 201000010374 Down Syndrome Diseases 0.000 claims 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 1
- 206010022998 Irritability Diseases 0.000 claims 1
- FFDGPVCHZBVARC-UHFFFAOYSA-N N,N-dimethylglycine Chemical compound CN(C)CC(O)=O FFDGPVCHZBVARC-UHFFFAOYSA-N 0.000 claims 1
- SEISMVVARRAVIM-UHFFFAOYSA-N N-[8-chloro-1-(1-pyridin-2-ylpiperidin-4-yl)-5,6-dihydro-4H-[1,2,4]triazolo[4,3-a][1]benzazepin-5-yl]-2-methylpropanamide Chemical compound ClC=1C=CC2=C(CC(CC=3N2C(=NN3)C3CCN(CC3)C3=NC=CC=C3)NC(C(C)C)=O)C1 SEISMVVARRAVIM-UHFFFAOYSA-N 0.000 claims 1
- NTUAPBORKZUYBH-UHFFFAOYSA-N N-[8-chloro-1-(1-pyridin-2-ylpiperidin-4-yl)-5,6-dihydro-4H-[1,2,4]triazolo[4,3-a][1]benzazepin-5-yl]acetamide Chemical compound C(C)(=O)NC1CC=2N(C3=C(C1)C=C(C=C3)Cl)C(=NN2)C2CCN(CC2)C2=NC=CC=C2 NTUAPBORKZUYBH-UHFFFAOYSA-N 0.000 claims 1
- AXCYSQYUKYXIEG-UHFFFAOYSA-N OC1Cc2nnc(N3CCC(CC3)c3ncccc3Cl)n2-c2ccc(Cl)cc2C1 Chemical compound OC1Cc2nnc(N3CCC(CC3)c3ncccc3Cl)n2-c2ccc(Cl)cc2C1 AXCYSQYUKYXIEG-UHFFFAOYSA-N 0.000 claims 1
- 208000021384 Obsessive-Compulsive disease Diseases 0.000 claims 1
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical group C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 claims 1
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims 1
- GXBMIBRIOWHPDT-UHFFFAOYSA-N Vasopressin Natural products N1C(=O)C(CC=2C=C(O)C=CC=2)NC(=O)C(N)CSSCC(C(=O)N2C(CCC2)C(=O)NC(CCCN=C(N)N)C(=O)NCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(CCC(N)=O)NC(=O)C1CC1=CC=CC=C1 GXBMIBRIOWHPDT-UHFFFAOYSA-N 0.000 claims 1
- 102000002852 Vasopressins Human genes 0.000 claims 1
- 108010004977 Vasopressins Proteins 0.000 claims 1
- KBZOIRJILGZLEJ-LGYYRGKSSA-N argipressin Chemical compound C([C@H]1C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CSSC[C@@H](C(N[C@@H](CC=2C=CC(O)=CC=2)C(=O)N1)=O)N)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCCN=C(N)N)C(=O)NCC(N)=O)C1=CC=CC=C1 KBZOIRJILGZLEJ-LGYYRGKSSA-N 0.000 claims 1
- 208000029560 autism spectrum disease Diseases 0.000 claims 1
- 230000003542 behavioural effect Effects 0.000 claims 1
- 230000036772 blood pressure Effects 0.000 claims 1
- 210000003169 central nervous system Anatomy 0.000 claims 1
- 208000010877 cognitive disease Diseases 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 1
- 239000011737 fluorine Chemical group 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 150000004677 hydrates Chemical class 0.000 claims 1
- 208000013403 hyperactivity Diseases 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 1
- 230000001575 pathological effect Effects 0.000 claims 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 208000028173 post-traumatic stress disease Diseases 0.000 claims 1
- ICSNLGPSRYBMBD-CDYZYAPPSA-N pyridin-2-amine Chemical compound NC1=CC=CC=[15N]1 ICSNLGPSRYBMBD-CDYZYAPPSA-N 0.000 claims 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
- 230000028327 secretion Effects 0.000 claims 1
- 210000004999 sex organ Anatomy 0.000 claims 1
- 208000024891 symptom Diseases 0.000 claims 1
- 208000011580 syndromic disease Diseases 0.000 claims 1
- MYWDPCSTTDUJHZ-UHFFFAOYSA-N tert-butyl 4-(8-chloro-5-methoxy-5,6-dihydro-4H-[1,2,4]triazolo[4,3-a][1]benzazepin-1-yl)piperidine-1-carboxylate Chemical compound C(C)(C)(C)OC(=O)N1CCC(CC1)C1=NN=C2N1C1=C(CC(C2)OC)C=C(C=C1)Cl MYWDPCSTTDUJHZ-UHFFFAOYSA-N 0.000 claims 1
- AUJNTVRKPPXSPE-UHFFFAOYSA-N tert-butyl N-[8-chloro-1-(4-piperidin-1-ylpiperidin-1-yl)-5,6-dihydro-4H-[1,2,4]triazolo[4,3-a][1]benzazepin-5-yl]carbamate Chemical compound C(C)(C)(C)OC(NC1CC=2N(C3=C(C1)C=C(C=C3)Cl)C(=NN2)N2CCC(CC2)N2CCCCC2)=O AUJNTVRKPPXSPE-UHFFFAOYSA-N 0.000 claims 1
- BKANAFXTPKJRDD-UHFFFAOYSA-N tert-butyl N-[8-chloro-1-[4-(3-chloropyridin-2-yl)piperazin-1-yl]-5,6-dihydro-4H-[1,2,4]triazolo[4,3-a][1]benzazepin-5-yl]carbamate Chemical compound C(C)(C)(C)OC(NC1CC=2N(C3=C(C1)C=C(C=C3)Cl)C(=NN2)N2CCN(CC2)C2=NC=CC=C2Cl)=O BKANAFXTPKJRDD-UHFFFAOYSA-N 0.000 claims 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 1
- 125000001425 triazolyl group Chemical group 0.000 claims 1
- 229960003726 vasopressin Drugs 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4196—1,2,4-Triazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
- C07D223/02—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D223/06—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom not condensed with other rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
- C07D223/02—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D223/06—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom not condensed with other rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D223/08—Oxygen atoms
- C07D223/10—Oxygen atoms attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
- C07D223/14—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D223/16—Benzazepines; Hydrogenated benzazepines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains three hetero rings
- C07D487/14—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains three hetero rings
- C07D487/20—Spiro-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/12—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains three hetero rings
- C07D491/20—Spiro-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Epidemiology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Neurosurgery (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Pain & Pain Management (AREA)
- Psychiatry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU1700521A HU231206B1 (hu) | 2017-12-15 | 2017-12-15 | Triazolobenzazepinek |
| PCT/IB2018/060077 WO2019116324A1 (en) | 2017-12-15 | 2018-12-14 | Triazolobenzazepines as vasopressin v1a receptor antagonists |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL275084A IL275084A (en) | 2020-07-30 |
| IL275084B2 true IL275084B2 (en) | 2023-06-01 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL275084A IL275084B2 (en) | 2017-12-15 | 2020-06-03 | Triazolobenzazepines as vasopressin v1a receptor antagonists |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US11298363B2 (zh) |
| EP (1) | EP3724192B1 (zh) |
| JP (1) | JP7428647B2 (zh) |
| KR (1) | KR20200100111A (zh) |
| CN (1) | CN111479813B (zh) |
| AR (1) | AR113933A1 (zh) |
| AU (1) | AU2018385724B2 (zh) |
| BR (1) | BR112020011880A2 (zh) |
| CA (1) | CA3085562A1 (zh) |
| CL (1) | CL2020001564A1 (zh) |
| CU (1) | CU24630B1 (zh) |
| EA (1) | EA202091344A1 (zh) |
| HU (1) | HU231206B1 (zh) |
| IL (1) | IL275084B2 (zh) |
| JO (1) | JOP20200149B1 (zh) |
| MX (1) | MX2020006204A (zh) |
| PE (1) | PE20210671A1 (zh) |
| PH (1) | PH12020500548A1 (zh) |
| SG (1) | SG11202005299VA (zh) |
| TN (1) | TN2020000083A1 (zh) |
| TW (1) | TWI826406B (zh) |
| WO (1) | WO2019116324A1 (zh) |
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| TW202202495A (zh) | 2020-03-26 | 2022-01-16 | 匈牙利商羅特格登公司 | 作為ｇａｍｍａ－胺基丁酸Ａ受體次單元ａｌｐｈａ ５受體調節劑之㖠啶及吡啶并〔３，４－ｃ〕嗒𠯤衍生物 |
| WO2022135335A1 (zh) * | 2020-12-21 | 2022-06-30 | 上海济煜医药科技有限公司 | 三氮唑类三并环衍生物及其制备方法和应用 |
| HUP2100338A1 (hu) | 2021-09-29 | 2023-04-28 | Richter Gedeon Nyrt | GABAA ALFA5 receptor modulátor hatású biciklusos aminszármazékok |
| WO2023164710A1 (en) * | 2022-02-28 | 2023-08-31 | The Trustees Of Columbia University In The City Of New York | Avpr1a blockade to reduce social isolation-induced anxiety in females |
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| ES2056259T3 (es) | 1989-02-10 | 1994-10-01 | Otsuka Pharma Co Ltd | Derivados de carboestirilo. |
| FR2679903B1 (fr) | 1991-08-02 | 1993-12-03 | Elf Sanofi | Derives de la n-sulfonyl indoline portant une fonction amidique, leur preparation, les compositions pharmaceutiques en contenant. |
| DE69434032T2 (de) | 1993-07-21 | 2005-09-22 | Yamanouchi Pharmaceutical Co., Ltd. | Zwischenprodukt zur Herstellung von kondensierten Benzazepinderivate |
| WO1995034540A1 (en) | 1994-06-15 | 1995-12-21 | Otsuka Pharmaceutical Company, Limited | Benzoheterocyclic derivatives useful as vasopressin or oxytocin modulators |
| FR2740136B1 (fr) | 1995-10-24 | 1998-01-09 | Sanofi Sa | Derives d'indolin-2-one, procede pour leur preparation et les compositions pharmaceutiques les contenant |
| BR0110961A (pt) | 2000-05-19 | 2004-06-29 | Merck Patent Gmbh | Derivados de triazol |
| EP1307430B1 (en) | 2000-07-05 | 2005-09-28 | Ortho-McNeil Pharmaceutical, Inc. | Nonpeptide substituted spirobenzoazepines as vasopressin antagonists |
| AU2002224115A1 (en) | 2000-11-28 | 2002-06-11 | Yamanouchi Pharmaceutical Co., Ltd. | 1,4,5,6-tetrahydroimidazo(4,5-d)diazepine derivatives or salts thereof |
| MXPA04003358A (es) | 2001-10-12 | 2004-07-08 | Serenix Pharmaceuticals Llc | Antagonistas de vasopresina v1a de ?-lactamilo. |
| JP2005104838A (ja) | 2003-01-09 | 2005-04-21 | Tanabe Seiyaku Co Ltd | 縮合フラン化合物 |
| ATE349449T1 (de) * | 2003-02-19 | 2007-01-15 | Pfizer | Für die therapie geeignete triazolverbindungen |
| GB0303852D0 (en) * | 2003-02-19 | 2003-03-26 | Pfizer Ltd | Triazole compounds useful in therapy |
| GB0325021D0 (en) * | 2003-10-27 | 2003-12-03 | Pfizer Ltd | Therapeutic combinations |
| GEP20084571B (en) | 2003-12-22 | 2008-12-25 | Pfizer | Triazole derivatives as vasopressin antagonists |
| GB0400700D0 (en) * | 2004-01-13 | 2004-02-18 | Pfizer Ltd | Compounds useful in therapy |
| EP1632494A1 (en) | 2004-08-24 | 2006-03-08 | Ferring B.V. | Vasopressin v1a antagonists |
| CA2578370A1 (en) | 2004-08-25 | 2006-03-02 | Pfizer Inc. | Triazolobenzodiazepines and their use as vasopressin antagonists |
| EP1831197A2 (de) | 2004-12-31 | 2007-09-12 | Abbott GmbH & Co. KG | Substituierte oxindol-derivate, diese enthaltende arzneimittel und deren verwendung |
| MX2007011693A (es) | 2005-03-24 | 2008-03-11 | Abbott Gmbh & Co Kg | Derivados de oxindoles sustituidos, farmacos que contienen dichos derivados y uso de los mismos. |
| MX2007013986A (es) | 2005-05-13 | 2008-02-22 | Lexicon Pharmaceuticals Inc | Compuestos multiciclicos y metodos para su uso. |
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| MX2008000886A (es) | 2005-07-21 | 2008-03-18 | Hoffmann La Roche | Derivados de indol-3-il-carbonil-piperidin-benzoimidazol como antagonistas del receptor v1a. |
| CA2616937A1 (en) | 2005-07-29 | 2007-02-08 | F. Hoffman-La Roche Ag | Indol-3-yl-carbonyl-piperidin and piperazin derivatives |
| DE102006051796A1 (de) * | 2006-11-03 | 2008-05-08 | Merck Patent Gmbh | Triaza-benzo[e]azulenderivate |
| JP2010517966A (ja) | 2007-02-01 | 2010-05-27 | グラクソ グループ リミテッド | 摂食障害の処置のための１−オキサ−３−アザスピロ（４．５）デカン−２−オンおよび１−オキサ−３，８−ジアザスピロ（４．５）デカン−２−オン誘導体 |
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| JOP20150301B1 (ar) | 2014-12-09 | 2023-09-17 | Bayer Ag | بنزاميدات مستبدلة مع 3،1-ثيازول-2- يل |
| EP3261639B1 (en) | 2015-02-27 | 2022-08-24 | Verseon International Corporation | Substituted pyrazole compounds as serine protease inhibitors |
| PL3319959T3 (pl) | 2015-07-06 | 2022-02-14 | Alkermes, Inc. | Hetero-haloinhibitory deacetylazy histonowej |
| CN106349241B (zh) * | 2015-07-15 | 2020-04-21 | 上海翰森生物医药科技有限公司 | 具有hsp90抑制活性的三唑衍生物及其制备方法和应用 |
| EP3452470B1 (en) | 2016-05-03 | 2020-03-18 | Bayer Pharma Aktiengesellschaft | Amide-substituted phenyltriazole derivatives and uses thereof |
| US9988367B2 (en) | 2016-05-03 | 2018-06-05 | Bayer Pharma Aktiengesellschaft | Amide-substituted pyridinyltriazole derivatives and uses thereof |
| EP3452472A1 (en) | 2016-05-03 | 2019-03-13 | Bayer Aktiengesellschaft | Hydroxyalkyl-substituted heteroaryltriazole derivatives and uses thereof |
-
2017
- 2017-12-15 HU HU1700521A patent/HU231206B1/hu unknown
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2018
- 2018-12-12 TW TW107144774A patent/TWI826406B/zh active
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- 2018-12-14 EA EA202091344A patent/EA202091344A1/ru unknown
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| US20210260072A1 (en) | 2021-08-26 |
| TN2020000083A1 (en) | 2022-01-06 |
| AU2018385724B2 (en) | 2023-05-25 |
| CL2020001564A1 (es) | 2020-11-06 |
| TW201938170A (zh) | 2019-10-01 |
| HUP1700521A2 (en) | 2019-06-28 |
| CU24630B1 (es) | 2022-12-12 |
| CU20200048A7 (es) | 2021-03-11 |
| JP7428647B2 (ja) | 2024-02-06 |
| JOP20200149B1 (ar) | 2022-10-30 |
| JOP20200149A1 (ar) | 2020-06-10 |
| SG11202005299VA (en) | 2020-07-29 |
| CN111479813B (zh) | 2023-03-21 |
| WO2019116324A1 (en) | 2019-06-20 |
| IL275084A (en) | 2020-07-30 |
| HU231206B1 (hu) | 2021-10-28 |
| KR20200100111A (ko) | 2020-08-25 |
| EA202091344A1 (ru) | 2020-09-09 |
| MX2020006204A (es) | 2020-08-27 |
| PH12020500548A1 (en) | 2021-01-25 |
| US11298363B2 (en) | 2022-04-12 |
| CN111479813A (zh) | 2020-07-31 |
| EP3724192A1 (en) | 2020-10-21 |
| AU2018385724A1 (en) | 2020-07-09 |
| AR113933A1 (es) | 2020-07-01 |
| BR112020011880A2 (pt) | 2020-11-24 |
| EP3724192B1 (en) | 2022-08-03 |
| PE20210671A1 (es) | 2021-04-05 |
| JP2021506821A (ja) | 2021-02-22 |
| CA3085562A1 (en) | 2019-06-20 |
| TWI826406B (zh) | 2023-12-21 |
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